Incorporation of 2'-amido-nucleosides in oligodeoxynucleotides and oligoribonucleotides as a model for 2'-linked conjugates.

Abstract:

:The functionalisation of oligodeoxynucleotides and oligoribonucleotides by incorporation of 2'-amido-2'-deoxyribonucleosides, possibly containing a reporter group via the 2'-amido bond, was examined. Therefore 2'-acetamido-ribonucleosides containing a small methyl group at the 2'-amido bond were synthesized as model compounds. In order to evaluate the influence of this 2'-modification on the hybridization capacities, 2'-acetamido-2'-deoxyuridine was incorporated in both RNA and DNA strands. The suitability of phosphoramidite chemistry for the introduction of this modified nucleoside was proven using laser desorption mass spectrometry of the final oligonucleotide. The presence of the 2'-modification destabilised both RNA-RNA, DNA-DNA and mixed duplexes. Therefore, it can be concluded that the 2'-acetamido group is not a good linker for attachment of reporter groups to oligonucleotides.

journal_name

Nucleic Acids Res

journal_title

Nucleic acids research

authors

Hendrix C,Devreese B,Rozenski J,van Aerschot A,De Bruyn A,Van Beeumen J,Herdewijn P

doi

10.1093/nar/23.1.51

subject

Has Abstract

pub_date

1995-01-11 00:00:00

pages

51-7

issue

1

eissn

0305-1048

issn

1362-4962

pii

4c0191

journal_volume

23

pub_type

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